Nitromethane → 1-Chloro-2-fluoro-4-(2-nitroethenyl)benzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloro-3-fluorobenzaldehyde (10 g, 63.07 mmol) and ammonium acetate (4.861 g, 63.07 mmol) in HOAc (50 mL) was added nitromethane (14.12 mL, 252.3 mmol) and the reaction mixture was heated to reflux (120° C. oil bath) for 18 h. The reaction was cooled and diluted with water. The reaction mixture was filtered and solids were purified by SiO2 chromatography eluting with a EtOAc/hexane gradient (0 to 5% EtOAc) to afford 1.736 g (13.65%) of (E)-1-chloro-2-fluoro-4-(2-nitrovinyl)benzene (86).

Provenance & Evidence